Nellie was the sister of Dermod O'Brien, the painter and friend of Osborne, and was a close friend of the artist. The present work was painted in 1887, the year Dermod O'Brien registered as a student at the Antwerp Academy where Osborne himself had been a pupil between 1881 - 1883. It seems that there was some sort of attachment between the sitter and the artist, and according to O'Brien's biographer, Lennox Robinson (op.cit. p.75), there was a possible intention to marry. Indeed in a photograph of Dermod O'Brien's own wedding, Osborne and Nellie stand side by side behind the bride. There is a certain warmth and informality in this portrait which is in keeping with other portraits of those he knew best, such as J.B.S.MacIlwaine (Coll.National Gallery of Ireland) and Stephen Gwynn (Private Collection).
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